#45 Donald J. Trump (2017-2021) Giving America The Bird

Donnie was born to a wealthy upper class family who made sure he had the best of everything, including the best military school when it turned out he was a bit of a turd.  His father was a big proponent of the tried and true parenting method of treating your kids like shit, which is probably why Donnie developed some fairly pronounced narcissistic and sociopathic tendencies.  Utilizing his daddy’s money and connections, as well as every legal loophole and shady business dealing known to humankind, Donnie built up a real estate empire worth millions, at least until the convoluted financial shell game he was playing came crashing down.  Not only did he lose millions of dollars, but also his super model wife. 

Undeterred, Donnie married a new super model and started suing everyone he knew before they could sue him.  He also started slapping his name on everything imaginable, a strategy that somehow eventually made him the star of an extremely popular reality TV show.  Now a living brand, Donnie became obsessed with his appearance and public image, which for some reason involved an epic combover and orange spray tan.  As a result, he morphed into a parody of himself, a germaphobe desperate for attention, but refusing to be touched.  His new super model wife wasn’t a fan of this version of him, so he just married a new one, a Slovenian model named Melanija Knavs.   

In 2016, Donnie ran for president, probably as part of some kind of get rich scheme.  Despite a propensity for shady dealings and unwanted groping, his strategy of waving his dick around, bullying, and lying about everything amazingly worked.  Apparently enough Americans were so sick of politics that just burning it all down seemed like a viable solution.  Donnie made everyone uncomfortable, but for a lot of people it was the kind of uncomfortable you feel when as a teenager someone flips off your dad and calls him a mother fucker.  Everyone was surprised by the victory, especially Donnie, who suddenly had to give up a lucrative TV career for a salary amounting to peanuts.  Deciding that his win proved he was some kind of Machiavellian genius, Donnie began governing in a manner best described as the random whims of a cranky toddler mixed with the ravings of your conspiracy loving racist uncle.  It was a complete shitshow, fueled by burger binges, late night Tweets, and an extremely distorted vision of reality.  Donnie didn’t give two shits about anyone but himself, and if that meant destroying even the foundations of American democracy, then so be it.  The saddest part was that Donnie saw himself as the good guy, a poor misunderstood soul whom everyone was out to get.        

Donnie lost his bid for re-election in 2020, though of course being Donnie, he completely refused to accept it, declaring the entire thing to be a fraud and inciting a mob to attack the U.S. Capitol building.  This led to him getting kicked off of nearly all social media and becoming the first president to ever be impeached twice.  His desperation to win re-election probably had nothing to do with the fact that once back in the private sector he would have to deal with a growing pile of debts, lawsuits, and possible criminal charges.  Today, Donnie is hiding out in a compound in Florida, plotting away on how he can get his ass elected president again in 2024.      

Image: https://commons.wikimedia.org/wiki/File:Donald_Trump_(17645083170).jpg

#44 Barack H. Obama (2009-2017) I Think I’m Awesome, You Should Too

Let’s get it out of the way first thing.  Barry is an asshole.  All of the presidents have been assholes.  That’s kind of been the point of all this.  Barry’s father, who was from Kenya, met his mother while they were in university together.  Despite already having a wife and two kids back in Kenya, Barry’s dad knocked up his mother and then married her.  Two years later he left Barry’s mother to go knock up and marry other women.  The man had a hobby.  Barry’s mom, not one to let shit get her down, re-married, this time to a dude from Indonesia.  Barry spent several years of his childhood living in Indonesia, eating dog and snake and playing with his pet monkey Tata, before getting sent back to the U.S. to live with his grandparents.  Money was tight, but thanks to student loans and scholarships, Barry got to go to some of the best universities in the country.     

Barry experimented with alcohol and drugs a bit growing up, but spent most of his time playing basketball, listening to disco music, driving around in his rust bucket car, smoking cigarettes, and collecting comic books.  While in law school, Barry met his future wife, Michelle Robinson, who just so happened to also be his supervisor.  After law school, Barry took a job teaching law.  He also got involved in state politics and wrote two autobiographies about how awesome he was.  The second autobiography helped propel Barry into national politics, and also allowed him to finally pay off his student loans, four years before getting elected president.  In 2008, Barry ran for president on a message of hope, change, and that President Dubya was the worst person ever, much of it delivered via clever internet memes.  The strategy worked and Barry won the election.  

Barry’s presidency mostly consisted of playing golf, sneaking smokes outside, blaming Dubya for practically everything, and pointing out positive statistics even though nobody really felt all that positive about them.  Soon after his election, Barry was awarded the Nobel Peace Prize.  To celebrate, he kept the U.S. in a state of war throughout his presidency.  Barry was great at campaigning for president, but not so good at actually being president.  Barry was a man of strong convictions, which is a nice way of saying he didn’t know how to compromise.  When people disagreed with him, he would become a bit of a jerk, standoffish and condescending, which for some reason didn’t make people see things his way.  It probably didn’t help that he would often give unwanted advice on the best way to carry out mundane activities, such as shaking hands.  When Barry was elected president, half the country loved him and half hated him.  By the end of his presidency, half still hated him and the other half was just moderately okay with him.  For Barry, this was of course totally somebody else’s fault.     

After leaving the White House, Barry said his main goals were to get his driver’s license back and learn how to use a phone newer than a Blackberry.  Barry got a taste of his own medicine via his successor blaming everything wrong with the country on him, which might be why his wife became good friends with former President Dubya.  In retirement, Barry has done what he does best, writing memoirs about himself.  Proving he’s the first president who knows how the internet works, he has also started producing Netflix documentaries and hosting a podcast with Bruce Springsteen.  Barry is still alive today, undoubtedly sure of himself.

Image: https://commons.wikimedia.org/wiki/File:Barack_Obama_profile_picture.jpg

#43 George W. Bush (2001-2009) Why Won’t Daddy Love Me?

Dubya was born into an aristocratic family where his father was away most of the time making money.  His mother raised him and his siblings in the aristocratic fashion of disciplinary slaps and heated competitions for her love.  Like many children, Dubya became rebellious in his college years.  God only knows why.  Since his family was a bunch of preppy wasps, this involved him becoming a drunken redneck lout.  College age Dubya was later described as John Belushi in Animal House without the class.  Despite these antics, Dubya graduated with a degree in business, avoided the draft by joining the Texas National Guard, and then went into the oil business. 

The oil business did not work out well for Dubya, probably because he had put his amateur college drinking days behind him and had moved on to being a truly professional alcoholic.  In polite terms, Dubya was a wayward soul.  In real terms he was arrested three times for drunk in public, drunk driving, and stealing a Christmas wreath.  He also once challenged his father to a fist fight.  To put it bluntly, the man had daddy issues.  If he had been born a girl he probably would have ended up being a stripper.  Moving on from oil, Dubya became a part owner of a Major League Baseball team, where his drinking was less of a liability.  It was at this time that he met Laura Welch at a barbeque.  She put an end to Dubya’s hijinks.  The pair got married and she forced him to sober up and go to church.  Having a lot of extra time now that he wasn’t drunk 24/7, Dubya decided to go into politics, a move that led him to running for president in 2000.   

Dubya won the election thanks to a combination of pretending to be stupider than he actually was, helped along by his shitty public speaking skills, and poorly designed ballots.  The fact that his opponent had the charisma of piece of wood in a fancy suit didn’t hurt either.  Dubya was an authoritarian by nature, and though America was a democracy, the White House was a dictatorship.  Everything from Dubya’s early bedtime to the length of women’s skirts was strictly regulated.  Dubya spent most of his presidency being extremely paranoid about terrorists, dancing in the whitest fashion possible, making up somewhat clever nicknames for everyone he met, and taking overly long vacations to his ranch where he spent his free time clearing brush.  Hoping to impress his father, Dubya started hanging out with President Poppy’s old friends and invaded a country for no good reason.  This did not work out well.  Dubya was one of the most loved presidents at the start of his presidency, allowing him to get re-elected in 2004, but a hurricane, endless, war, and a financial collapse led to him being the most despised president by the time he left office. 

When Dubya left the White House he quietly disappeared, preferring to be out of the limelight except for a few public speaking appearances.  With all the brush on his ranch cleared during his presidency, Dubya had to find a new hobby for his retirement.  He settled on oil painting.  Dubya’s paintings tended to focus on portraits of world leaders, dogs, and several of himself naked in the shower and bathtub.  Dubya is still alive today, painting like a first year art student and jealously guarding his most prized possession, a photo of him with the band ZZ Top. 

Image: https://commons.wikimedia.org/wiki/File:George_W._Bush_during_presentation_of_Michael_A._Monsoor%27s_Medal_of_Honor.jpg